Sodium borohydride → 6-(Hydroxymethyl)-3-methyl-1-(2-methylpropyl)-5-(2-thienylmethyl)-thieno[2,3-d]pyrimidine-2,4(1h,3h)-dione

HRID 379596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379596
[BH4-].[Na+].[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11](SC3SC=CC=3)=[C:12]([CH:14]=[O:15])[S:13][C:7]=2[N:6]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:5]1=[O:26]>CO.O>[OH:15][CH2:14][C:12]1[S:13][C:7]2[N:6]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:5](=[O:26])[N:4]([CH3:3])[C:9](=[O:10])[C:8]=2[C:11]=1[CH2:14][C:12]1[S:13][CH:7]=[CH:8][CH:11]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 183665901,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-5-(thien-2-ylthio)-thieno[2,3-d]pyrimidine-6-carboxaldehyde

Produkt 1

HCID 183665956-(Hydroxymethyl)-3-methyl-1-(2-methylpropyl)-5-(2-thienylmethyl)-thieno[2,3-d]pyrimidine-2,4(1h,3h)-dioneAusbeute 104,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.06 g) was added to 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-5-(2-thienylthio)-thieno[2,3-d]pyrimidine-6-carboxaldehyde (0.25 g) in methanol (25 ml) and the mixture was stirred for 24 hours. The reaction was diluted with water (30 ml) and was then extracted with ethyl acetate (3×50 ml). The organic phases were washed with brine and dried over magnesium sulfate, filtered and evaporated to leave a green oil. Purification by chromatography (1:4 ethyl acetate:isohexane) gave the subtitle compound as a yellow foam (0.125 g).

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate (3×50 ml)
  2. washThe organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto leave a green oil
  7. customPurification by chromatography (1:4 ethyl acetate:isohexane)

Quellen und Nachweise

ORD-Eintrag
ord-4345ed6075214854b0da1b7f053b2cf0
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300334B1

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